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Our dealership had 160+ computers and 75 printers in a workgroup environment with an antique server 2003 DHCP server, no internal DNS and no central management. I installed a new Dell R440 server with MS Server 2016. Following advice from this community I uninstalled the OS and reinstalled the Core version of Server 2016 and installed two VMs to server as domain controllers. I set up the DC to serve DNS and DHCP and created an Active Directory environment and joined all of our computers to the domain and created AD user accounts. I created two more Server 2012 VMs using licenses I already had. One became my Spiceworks server and the other became a file/print server. I moved our files onto the file server and set up folder redirection for a subset of my users. I added a couple of printers and installed them to client machines using Group Policy Objects. I created GPOs to limit logins to certain machines to specific users/groups. I created OUs for each of our departments and have created a number of GPOs to assign file shares to users, create desktop shortcuts, modify IE settings, and some other things. Prior to this experience I had little or no knowledge of AD, GPOs, DHCP, DNS or VMs. All of this was learn-as-you-go for me and I got a lot of great tips from folks on this forum, thank you. I'm sure I did some things wrong (I never quite properly figured out DFS, and am still learning about the best way to use GPOs to maintain workstations, etc.) but I learned a heck of a lot and had a lot of fun doing it. I'd say the biggest challenge was working at the periphery of my sphere of knowledge without somebody to confer with directly when there was a question. I would enjoy this same experience in a team environment where there was a support system.